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Orleans Pet Friendly Vacation Rentals

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    Travellers to Orleans are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    27 Matching Rentals in OrleansView all 211 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    $1475-$2075 Rates include all charges. No hidden fees! This delightfully redone 2.5 bedroom/1.5 bath home located in a sought-after East Orleans location is bright and open with an unbeatable location! The front door leads directly into a large living room cooled by both a ceiling fan and window...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    AT SKAKET BEACH! This charming renovated 1927 Cape has ample room for 6, a master bedroom with a vaulted ceiling and a private half-bath, plus a lovely wraparound porch with hammock. The sunny interior features newly-painted floors, comfy furnishings throughout and excellent amenities, including...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly-furnished home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association tennis courts or deepwater...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    20 Deerwood Lane, East Orleans, MA (ID# 120896) 2017 Season! Wonderful Home in East Orleans with central A/C. Walk to restaurants or Sundae School after a relaxing day at Nauset Beach. This dog friendly (with homeowner approval) home features lots of room with 4 bedrooms, hardwood floors...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    244 Tonset Road, East Orleans (ID#125800) 2018 Season! Adorable vacation rental located in East Orleans. This property has a screened porch overlooking the private back yard located in a nice neighborhood equidistant to Nauset Beach on the Atlantic Ocean and Skaket Beach watch the sun set over...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    28 Kings Way, Orleans MA (ID# 95117) 2017 Season! Adorable 3 Bedroom, 2 Bath Cape style home close to Skaket Beach. Convenient to Nauset Beach, Orleans Town Center, and the bike trail. Main level includes large living area, eat in kitchen, bedroom with two twins and full bath. Second level has main...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sweeping Bay Views, Privacy, Two Full Kitchens (Pets Considered) Peak Summer Weekly Rates: $4,300 - $4,500 Rents Saturday - Saturday during peak season This unique vacation home is nestled between Rock Harbor to the east and Skaket beach to the west. The home has its own private boardwalk across...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    East Orleans; magnificent updated historic home, heated pool, A/C, perfect family vacation; Sleeps 13 Peak Summer Weekly Rates: $9,500 - $11,000 Rents Saturday - Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home The interior of this beautiful 1920 Orleans...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Classic Nauset Heights 3 Bedroom home sitting directly on the bluff with magnificent views of Nauset Beach, the Atlantic Ocean, Nauset Marsh, Coast Guard Light, and Fort Hill. Short walk to bay and ocean beaches. Vintage cottage character in unbelievable location. Great value for view. Full...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    NEW LISTING!!! This is a well appointed 3000 square foot home in South Orleans, minutes from Rt. 28. Easy access towards Nauset and Skaket beach or Pleasant Bay. The downstairs includes a master suite with King bed and ensuite, full open kitchen and dining room, kids play room, laundry / mud room....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This beautiful Cape Cod home sits on Barley Neck, which is small peninsula just a few minutes drive to Nauset Beach. It is surrounded by Meeting House Pond and Little Pleasant Bay. This area is harbored from the Atlantic Ocean by Pochet Island. From this location, you are walking distance to the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This Pet friendly home is located just 0.8 miles from Nauset Beach. Enter into a charming, warm home that offers two spacious living areas. One is a bright great room with cathedral ceilings, sectional seating, big screen t.v and game table. Head into the living room where you will find a cozy...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Walking distance to Ponds, Passive Solar This 3 Bedroom 2.5 bath retreat with Central AC is hidden away down a semi private drive in East Orleans. It has large sliding glass doors down one side of the home off the living room offering lots of light. Mid century modern decor fills this clean lined...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxury 6 BR Home W/ 60 Foot Private Pool1 / 23
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
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    • Sauna
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    This warm and inviting 6 bedroom, 4 bath home sprawls over 4 stories of comfortable rooms with spacious, open living areas and a private, fully fenced back yard. Perfectly located in South Orleans, the house is just minutes from the Lower Cape villages of Chatham, Brewster and Orleans. A beautiful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    61 Captain Linnell Road, Orleans, MA (ID# 100002) Near Skaket Beach 2017 Season! Spacious, beautifully updated, dog friendly home near Skaket Beach on Cape Cod Bay. Large granite and stainless kitchen opens to dining area, living area and office. Sliders to deck, brick patio, back yard and fire...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
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    Spacious 4 Acre private waterfront estate located in the prestigious and secluded Snow Point Association with private steps down to the water. Snow Point is a small peninsula of land in Orleans bordered by Rachel Cove, Town Cove and Woods Cove. You'll experience 180-degree views of the water from...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2 bedroom 1 bath apartment with separate private entrance, driveway and deck. Living room, kitchen, and laundry. Queen bed in one room and a double bed in the other room. Optional air mattress can be set up in living room to sleep 2 more if needed. Window AC units in bedrooms. Ceiling fans in...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Meticulous Modern East Orleans Home, Water Views, Pets Considered Peak Season Weekly Rate: $8,000-$8,500 Rents from Sunday to Sunday during peak weeks The height of modern luxury in East Orleans, this home has tremendous views of Nauset Inlet and the Atlantic Ocean beyond. The first thing you'll...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Recently renovated home on Crystal Lake in Orleans! (Linens Included, Pets Considered) Peak Summer Weekly Rates: $3,500 - $3,700 Rents Saturday to Saturday during peak season NEW Listing for 2018! Updated Waterfront Home on Crystal Lake, with air conditioning, in the heart of Orleans. Crystal Lake...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    50 Keziahs Lane Orleans 4 Bedrooms 3 Full Baths Nauset Beach not far away. 2017 Season! Charming, peaceful and gracious 4BR/3BA home on a dead-end private road! On two semi-secluded acres abutted by conservation land, and 200 yds from bay inlet and nature reserve with a mile of waterfront, deeded...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    This adorable cottage is situated on the bluff overlooking Nauset Beach, on the water on Nauset Heights. Short walk to both inland waters and Nauset Outer Beach. This property has panoramic ocean, beach and water views. Property type: House Room type: Entire home/apt Accommodates: 8 Bathrooms:...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located in the desirable Captain Linnell area of Orleans, this home offers one floor living, a large yard, and is pet friendly! This lovely 3 bedroom, 1 bath home is just .3 miles to beautiful Skaket Beach and features cable TV, wireless internet and air conditioning! The Master Bedroom, just off...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    #506 Shipmates Beach House: 200-yards down gravel road to Private section of Nauset Beach. Roof Deck! Water Views! Large manicured yard for outdoor games. Once at the private association beach entrance (just 3-minutes walk) it is another beautiful and short 7-minute walk over the Nauset marsh to...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    #501 Viking Cottage: New renovation, sunny secluded home with view & access to saltwater. Enjoy the pleasures of a waterfront property -- Wake up to views of a peaceful Pleasant Bay inlet from this sun-filled, modern 3-bedroom cottage in the woods. Launch your kayak or canoe to explore beautiful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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